Harold Grinspoon decided to splurge 10 years ago and bought a boat. While other multimillionaires sail 150-foot yachts, Grinspoon launched a 17-foot whaler, which his wife described as a “floating bathtub.” It sank not long afterward.

It was one of the last times he bought a big gift for himself. “I don’t like to spend my money frivolously,” said Grinspoon, 83, of Longmeadow.

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He made his millions in the real estate business and
has since used that expertise in philanthropy, funneling contributions from his foundation to programs that deliver results and have the potential to grow. Since its founding in 1993, the Harold Grinspoon Foundation of West Springfield has given more than $120 million to Jewish causes, identifying undervalued assets in the Jewish community and revitalizing them through partnerships that bring in more money and resources.

His most recent initiatives over the past few months illustrate this approach. One pilot program, called PJ Promise, aims to secure endowments to ensure the future of his foundation’s best known program, PJ Library — named for pajamas children wear while being read to in bed. It delivers free, Jewish-themed books to 100,000 families across North America, with a goal of educating and instilling pride in Jewish heritage and culture.

Another program, Life and Legacy, provides matching grants for Jewish institutions to use to attract bequests from Jewish senior citizens.

“If you’re an entrepreneur, you’re a creative thinker in making money,” Grinspoon said. “Why can’t you use the same standards in giving it away?”

He grew up in a poor, secular Jewish household in Newton, long before the city became a hub for Jewish life. He recalled being one of few Jews in his neighborhood, and was often subject to anti-Semitic remarks.

After dropping out of college in 1951, Grinspoon worked odd jobs before persuading an in-law to loan him money to buy a run-down two-family home in Agawam. He used the money he made from selling that property to purchase a four-family home, then a six-family, then a 10-unit building.

In the 1960s, Grinspoon started the real estate company that became Aspen Square Management in Springfield. Today, it manages properties in 15 states.

For many years, Grinspoon was more concerned with making money than giving it away. Then he met his third wife, Diane Troderman, and that changed.

Together they expanded their charitable giving, starting with inner-city education in Springfield, then endowments to Massachusetts General Hospital after Grinspoon was treated for throat cancer there in the late 1980s.

Grinspoon and Troderman soon began to focus on Jewish causes.

Although both were raised in secular homes, persistent anti-Semitism, threats against Israel, and the legacy of the Holocaust convinced them of the importance of a strong Jewish community.

They started in the Soviet Union, where religious practice was outlawed and anti-Semitism institutionalized. Grinspoon and Troderman made several trips to the communist nation beginning in the 1980s, traveling the paths of the old Silk Road, hiking the mountains of modern-day Kazakhstan, and smuggling prayer shawls and yarmulkes to oppressed Jewish communities.

They passed the items clandestinely to Soviet Jews in train stations and cafes, often without speaking.

“It was like something out of an Ian Fleming novel,” Grinspoon recalled.

Grinspoon said they also saw the same need to promote Jewish identity and education in the United States, where assimilation into a secular society had dulled a generation’s understanding and appreciation of Jewish thought and culture.

Since its founding, the Grinspoon Foundation has been a major contributor to Jewish programs in the United States, including the Partnership for Excellence in Jewish Education, which supports Jewish day schools; Taglit Birthright Israel, which provides free trips to Israel; and Hillel: The Foundation for Jewish Campus Life, which fosters Jewish life at colleges and universities.

The foundation also supports Jewish summer camps by providing matching grants to camps to help raise money from other philanthropists. Nearly 100 camps have used Grinspoon’s $22 million to secure another $110 million in donations and legacy endowments.

In Western Massachusetts, the foundation supports five Jewish day schools. It founded and funds the annual Pioneer Valley Jewish Film Festival. It runs a Jewish teen philanthropy program. Last year, the foundation also launched Voices and Visions to commission established and up-and-coming Jewish artists to create artwork inspired by quotations from Jewish authors and figures such as Louis Brandeis, Franz Kafka, and Anne Frank.

“In buying property, Harold looked for undervalued assets and we helped to turn them around,” said Troderman, 71. “In his head, whether it is literacy or Jewish camps, his philanthropy is about undervalued assets.”

The PJ Library is the organization’s flagship program. it began in 2006 in Western Massachusetts with 200 families. Grinspoon said the hope at the time was to expand to 5,000 families within five years.

It grew a little faster than that. In 2012, Grinspoon hand-delivered the library’s 3 millionth book to a girl in New Jersey.

Today, there are PJ Library families in Mexico, Argentina, and Australia. In 2013, Grinspoon and Troderman will travel again to Russia to lay the groundwork for PJ Libraries in that country.

In Israel, a sister program called Sifriyat Pijama sends books directly to 4,000 preschools, nearly 40 percent of all such schools in Israel. It’s cosponsored by the Grinspoon Foundation and the Israeli Ministry of Education.

So why does Grinspoon, so cautious with his money, spend so much on Jewish education?